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Volumn 53, Issue 48, 1997, Pages 16377-16390

Synthesis of amino sugars through a highly diastereoselective dipolar cycloaddition. Enantioselective synthesis of the carbohydrate segment of Sch 38516

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; ANTIFUNGAL AGENT; FLUVIRUCIN B1; SCH 38516; UNCLASSIFIED DRUG;

EID: 0030782344     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01023-5     Document Type: Conference Paper
Times cited : (23)

References (65)
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    • Oppolzer, W.; Radinov, R. Tetrahedron Lett. 1988, 29, 5645-5648 and references cited therein.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5645-5648
    • Oppolzer, W.1    Radinov, R.2
  • 29
    • 33747849809 scopus 로고
    • For examples of stereochemical control in additions to C=O groups, where chelation of Zn to an α-alkoxy group is proposed, see: (a) Gensler, W. J.; Johnson, F.; Sloan, A. B. D. J. Am. Chem. Soc. 1960, 82, 6074-6081.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 6074-6081
    • Gensler, W.J.1    Johnson, F.2    Sloan, A.B.D.3
  • 46
    • 0342930309 scopus 로고    scopus 로고
    • note
    • 4, EtOAc, MeCN.
  • 48
    • 0343365596 scopus 로고    scopus 로고
    • note
    • DeShong's original conditions are: 30 equivalents of vinylene carbonate, 95 °C, 72 h (see ref 20). It is noteworthy that use of five equivalents of the carbonate (condition used in this study) allows for a less cumbersome isolation of the cycloadduct.
  • 51
    • 0019959484 scopus 로고
    • and references cited therein
    • (c) Vasella, A.; Voeffray, R. Helv. Chim. Acta. 1982, 65, 1134-1137 and references cited therein.
    • (1982) Helv. Chim. Acta. , vol.65 , pp. 1134-1137
    • Vasella, A.1    Voeffray, R.2
  • 54
    • 37049117646 scopus 로고
    • Bjorgo, J.; Boyd, D. R.; Neill, D. C. J. Chem. Soc, Chem. Commun. 1974, 478-479. The preference for the Z isomer is, presumably, so that the disfavored steric interaction between the benzyl group and the dioxolane ring can be avoided.
    • (1974) J. Chem. Soc, Chem. Commun. , pp. 478-479
    • Bjorgo, J.1    Boyd, D.R.2    Neill, D.C.3
  • 55
    • 0010396235 scopus 로고
    • The chiral aldehyde used to synthesize 19 was prepared according to the method of Fuganti: Fuganti, C.; Grasselli, P. Chem. Ind. (London) 1977, 983.
    • (1977) Chem. Ind. (London) , pp. 983
    • Fuganti, C.1    Grasselli, P.2
  • 61
    • 0343365595 scopus 로고
    • Ph. D. Thesis, University of Maryland, p.26
    • (a) Leginus, J. M. Ph. D. Thesis, 1985, University of Maryland, p. 26.
    • (1985)
    • Leginus, J.M.1
  • 65
    • 0343801316 scopus 로고    scopus 로고
    • note
    • Reaction through the alternative conformer is predicted not to be competitive; this conformer suffers from steric and electron-electron repulsion, as illustrated below Chemical equations presented.
    • , vol.32


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